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Windows 7: Difficult decision or much ado about nothing?

Along with operating system expertise I figure that many posters here use web hosting of some sort and maybe have some good advice on the following.

A few years ago an acquaintance that I've known for years online offered me free web hosting on Dreamhost with whom he has an arrangement for multiple accounts. In other words, there are 20 others (each with their own website) who are on the account and I'm one of them. It's fairly easy, I've got a CPanel as I previously had on a paid host years before, can do all the organizing, etc., that one needs to do.

Recently, the person told me he's going to let go of the Dreamhost account by the end of this year. He said that I can move the website to his own servers - he now has his own web design company - and that I can likewise use it for free. So, I began to ask some questions here and there and basically his reply amounts to the following which I will directly quote:

"Once you successfully transfer over your entire website, including the databases, and hook everything up so it's all working on the new server and tested [and you can view it there and test without changing any public facing settings by the way, I'll let you figure out how to do that also -- hint: it involves your hosts file in windows]; then yes, you need to change your domain's DNS settings so that the public accesses your website on the new server and it should provide a seamless transition.

You'll have to do the transfer yourself, hook everything up yourself, and test everything is working yourself [migrate and test your website -- yourself], and adjust your domain's settings yourself."

Basically: I am willing to provide free & excellent quality hosting and minimal support, but not to manage or migrate your website for you, or teach you how the internet works."

Now, to my recollection I have never asked him to manage the website or teach me how the internet works. Add to this the "minimal support" aspect and I begin to wonder how "free" the free is going to be. Not in terms of a surprise fee or anything like that since I once offered to pay and he said he wouldn't accept it, I'm thinking free in terms of if some problems came up how much support would there be to correct whatever.

Some of you with your experience might be saying, "Free webspace on a good server and with minimal support? No problem, I'll take it, go ahead and do whatever else you have to do and I'll run the whole show from here".

Thing is, I personally do not have the knowledge to transfer, hook, test, and adjust domain settings. Usually that's done by the hosting company and while I am more than aware that the server space is free and thus cannot be asking for what I would ask for in a paid account I'm wondering if in the long run I'm better off just getting another paid hosting account and not have to worry about support problems.

The other side of this is if I'm making a mountain out of a molehill, that what he's saying about transfer, hook, etc., is really not that difficult. Well, I got as far on the new CPanel to make a database for a small forum and after some reading around felt confident enough to transfer it. But now with everything else, including setting up the domain name in the new server, routing the url there and everything else I'm just thinking if a paid host isn't just the quicker solution to this.

I don't know about the ins and outs but from a mission critical stand point if the system goes down will it effect you in a financial way and can you and your friend get the system back up and running quickly? If the answer is yes then you need a web host of your own. If it goes off for a day or two whilst he fixes the server and does not matter then your friend is the place to be.
My 2 pence.

Yes, if you can be down for a day or two (say his server fails or power is out in the area after a storm etc.) then it is OK for you to be with your friends site. If you run a store or provide a service and are down for a few days it will lose you business and spoil your web site's reputation.

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